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Synfacts 2016; 12(06): 0589
DOI: 10.1055/s-0035-1562190
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation Reaction

Rezensent(en):
Mark Lautens
,
Alvin Jang
Cotman AE, Cahard D, Mohar B * University of Ljubljana and National Institute of Chemistry, Ljubljana, Slovenia; Université et INSA de Rouen, Mont Saint Aignan, France
Stereoarrayed CF3-Substituted 1,3-Diols by Dynamic Kinetic Resolution: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation.

Angew. Chem. Int. Ed. 2016;
55: 5294-5298
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Publikationsverlauf

Publikationsdatum:
17. Mai 2016 (online)

 
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Key words

transfer hydrogenation - ruthenium catalysis - asymmetric reduction

Significance

In this report, ruthenium-based transfer hydrogenation catalysts are described. The catalysts exhibit impressive turnover numbers with excellent enantioselectivities for the selective reduction of CF3-substituted 1,3-dicarbonyl compounds. The substrates include benzo-fused cyclic ketones which undergo reduction to furnish one stereoisomer.


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Comment

Transfer hydrogenation (TH) reactions are milder and safer alternatives to metal-on-carbon-based hydrogenation reactions. Although the scope is usually limited to the reduction of carbonyls, TH avoids the use of highly pressurized systems. These reported ruthenium-based transfer hydrogenation catalysts are notable achievements in this field.


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